Jangan Gosipin Aja: Bridgerton Meets Gossip Girl: 5 Couples That Would Work (& 5 That Wouldn't)

The show Bridgerton has been publicized as the Regency-era Gossip Girl, but is Lady Whistledown more effective and saucier than Ms. XOXO? If there ever was a crossover between the two timelines and the characters were brought together in one society, it’d be quite the party.

This begs the question, who’d date who? Would Penelope aka Lady Whistledown scoff at the socially insecure Dan Humphrey, the real Gossip Girl? Would Serena van der Woodsen find love with a Bridgerton brother? Here are 5 couples that would totally be a thing if the two universes met, and 5 couples who have no chance

10 Would Work: Eloise And Dan

Dan Humphrey and Eloise Bridgerton have quite a lot in common; they both look down upon members of their elitist social circle, they are worldly and do not shy away from calling a spade a spade. Dan is someone who seeks a relationship founded on friendship and mutual respect, which was why he could never accept the fact that Serena always considered him an ‘outsider,’ although he always referred to himself as one.

Eloise, in a way, is the outsider in her social strata because she challenges almost every dysfunctional norm there is and chances are these two would hit it off almost instantly.

9 Would Not Work: Chuck And Marina

One could see why Marina Thompson and Chuck Bass would be attracted to one another; they both in a way, seek power and prominence. They are also believers in forging their own way in the world, however, they are both simply too self-serving to sustain a relationship that is albeit going to be a challenging one, given their personal hang-ups.

Marina is someone who seems to long for true love and the only way Chuck can have a functional, long relationship is if his partner is ready to look past all his flaws like Blair did on the show.

8 Would Work: Nate And Benedict

There are aspects of their arc which are really similar; they are both from privileged backgrounds and have had to unlearn and disassociate from the toxic patterns of their social circles. Nate and Benedict are both grounded, logic-driven and know when to ditch sentimentality especially when it becomes a burden. As partners they value integrity and transparency above everything else.

Benedict seeks a loyal, compatible partner he could respect for who they are and Nate, too values compatibility and honesty. Let's not forget, that he has broken up with quite a few people over their lies. One could see why they would be attracted to each other since they share so many ideals.

7 Would Not Work: Blair And Benedict

Blair is everything Benedict Bridgerton despises about high society; she’s a bully, she’s elitist, and can be quite cruel to anyone who she thinks is challenging her privilege. A match between the two would be nothing short of a disaster. To be fair, Blair is a victim of her own society, she has simply been brought up to be self-serving.

However, Benedict is also a product of the one-percenters and he has managed to unlearn whatever he has been taught as a child and simply has enough belief in his own convictions and merits.

6 Would Work: Daphne And Nate

Any Gossip Girl fan would pick someone like Daphne for Nate in a matchmaking scenario; as Gossip Girl progressed, Nate became more and more sensitive and compassionate as a friend and partner.

He was able to steer away from the toxic patterns of his teenage days and came to value honesty and meaningful exchange in relationships. Daphne has some very similar needs from her partner, she appreciates loyalty and has the perseverance to stand by her partner during a crisis, and would be a terrific match for Nate.

5 Would Not Work: Jenny And Simon

Jenny Humphrey and Simon Basset need to put a lot of work on the personal front to deal with their inner demons before they could embark on a successful relationship. They are alike in many ways, they’re both quite icy and can end up taking themselves too seriously. And though Jenny and Simon can really hit it off as friends, a romance between them would be a terrible idea.

Neither of them is a good listener and don’t always reflect on their own flaws, and a romantic bond between the two would be pretty disastrous.

4 Would Work: Penelope And Dan

Of course, a romantic alliance between the real Gossip Girl and Lady Whistledown would thrive for obvious reasons. Penelope and Dan have both felt excluded from the people around them and their attempt to launch a scathing attack on the very society they’re a part of, is at its core a retaliation against a culture they desperately want to fit into.

Neither of them had the courage to shun the society which has served them well at certain points (Penelope especially considering her privileged upbringing as a Bridgerton). But they would see and relate to the angst in each other and a romance between the two could easily blossom.

3 Would Work: Serena And Anthony

Both Serena van der Woodsen and Anthony Bridgerton are looking for the same kind of love, one that is based on friendship and compatibility. And despite having led privileged lives, their romantic demands are rather simplistic.

One could see how someone as gallant and straightforward as Anthony would make Serena happy; though Anthony is a bit hot-headed and wears his heart on his sleeve, Serena appreciates transparency and honesty in a relationship, and in a way, this match would be really perfect.

2 Would Not Work: Blair And Simon

Since both Blair Waldorf and Simon Basset refuse to own up to their personal hang-ups most of the times (and can even gaslight people unconsciously), they’d be a match made in hell, especially because they do not like being challenged. Though Simon is willing to grow and learn more about his partner’s needs and can even strive to be more accommodating, Blair is a total steam-roller, especially when it comes to her loved ones.

It’d be very tough for these two to put their differences and personal hang-ups aside and to commit functionally in a meaningful relationship for the long term.

1 Would Work: Daphne And Serena

Daphne and Serena could really be great together, especially because they share a very similar sort of personal arc. They are both from affluent backgrounds and yet, they're quite traditionalist when it comes to their romantic pursuits and value commitment immensely.

Serena has often been depicted as someone who doesn't do well in long-term relationships but it's important to note that she has always sought a stable, monogamous relationship. Daphne is also a believer in monogamy and they prioritize stability and compatibility, and most importantly they’re willing to work on the relationship despite several odds. Plus, they are really giving as partners which is why they get hurt too easily; if ever they embark on a relationship they'd be sensitive to each other's needs.

NEXT: Bridgerton Cast & Character Guide: What Else The Actors Have Been In